Brad Pitt's Love Life: A Timeline

Pitt dated Louis Walsh's mate Sinitta on and off for four years. Sinitta was in her heady pop star days, and Pitt even attended the 1988 Smash Hits Poll Winners Party with her.

Yes, there is some overlapping with Sinitta. The actor dated Mike Tyson's wife while she was married to him.

The Don't Tell Mom the Babysitter's Dead star took Pitt as her date to the MTV Movie Awards that year, only to famously ditch him halfway through the night for another guy. Ouch.

Pitt and Schoelen met on the set of horror movie Cutting Class. He popped the question, and they were engaged for three months in 1989, until she started dating the director of another movie she was working on, and dumped Brad. Ouch, again.

Pitt dated Daily, a popstar, and more importantly the voice of Tommy Pickles in Rugrats and Phoebe's Smelly Cat nemesis in Friends, for a short time after his split with Jill.

Pitt was 27 when he started dating his 17-year-old Too Young To Die? co-star Lewis. She said in 2010 about the relationship: "It amazes me that people are still fascinated that we went out for four years. I was a teenager at the time. It's a lifetime away. I was in my high-school years and it was a wonderful, loving relationship with a fun, smart guy. Then it was over and he went on to become incredibly famous."

Yes, another overlap…

Apparently after starring alongside Geena in Thelma & Louise, Pitta and Davis met up secretly in real life. That's according to Pitt's former roommate Jason Priestly.

Pitt and Newton dated briefly after they met on the set of Interview with the Vampire. They split amicably and are still friends, apparently.

Pitt proposed to Paltrow in 1996 after the couple met while filming Se7en two years earlier. Pitt referred to Gwyn as his "angel" and "the love of his life" in his speech at the Golden Globes. They called off their engagement seven months after he proposed. Gwyn said in 2015: "I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt! My father was devastated [when we split]. I was such a kid, I was 22 when we met. It's taken me until 40 to get my head out of my ass. You can't make that decision when you're 22 years old. I wasn't ready, and he was too good for me."

Pitt and his first wife Aniston met when their agents set them up on a blind date. After two years of dating, Pitt and Aniston got engaged and started planning their lavish, Hollywood wedding, which took place in July 2001 in Malibu and cost over $1 million. Everything was fine until 2004 when Pitt started filming Mr. & Mrs. Smith with Angelina Jolie. Nothing happened between Pitt and Jolie during filming, apparently, but Pitt did say later on that it was during this time that he and Jolie fell in love. In January 2005, Pitt and Aniston announced they were getting divorced.

Pitt and Jolie were together for 12 years, married for two, and have six children together. Angelina filed for divorce from Brad on September 19, 2016.